


Life Starts All Over Again When it Gets Crisp in the Fall

by thnksfrthwilliam



Category: Supernatural
Genre: Alternate Universe - College/University, Anal Sex, Cunnilingus, F/M, Gabriel Big Bang Challenge, M/M, Multi, Polyamory, Rimming, Stanford Era, Threesome, Threesome - F/M/M, Underage Drinking
Language: English
Status: Completed
Published: 2014-04-23
Updated: 2014-04-23
Packaged: 2018-01-20 13:14:27
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 17,504
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1511828
Author URL: https://archiveofourown.org/users/thnksfrthwilliam/pseuds/thnksfrthwilliam
Summary: <blockquote class="userstuff">
              <p>Sam and Jess are the all-American Power Couple on campus. Gabriel is a Gatsby-esque playboy. They meet at a party and there's a spark that none of them were expecting. What blooms from that meeting is something more than they could have predicted, but they're all incredibly happy with the outcome.</p>
            </blockquote>





	Life Starts All Over Again When it Gets Crisp in the Fall

There were two main subjects of gossip during the current semester at Stanford. The first was the resident power couple, Sam Winchester and Jessica Moore. Despite both being mere sophomores, they were the most talked about couple on the quad. Both gorgeous, both tall, and both exceptionally smart (even by Stanford’s standards), they were targets of huge amounts of envy and following that, huge amounts of gossip. Little of it was true, but they certainly didn’t mind the attention.

 

The second was Gabriel. Just Gabriel. Hardly anyone on campus knew his last name, he had made sure of it. Professors knew better than to utter it when taking roll and anyone who knew it (read: his housemate, Chuck Shurley) knew the dire consequences if they told a soul (read: trash duty for a month). He was an enigma of sorts – everyone knew of him, but hardly anyone actually knew him. If you asked a thousand students walking through campus about Gabriel, they would all know exactly who you were talking about ( _He’s the senior who throws those hella rad parties right?_ ), but you’d be hard-pressed to find someone who could tell you what he was majoring in or what he did for fun or anything beyond the fact that he was a short, funny guy who liked to throw parties. And that was exactly how he wanted it.

 

It was no accident and certainly no surprise when the Power Couple ended up at the Enigma’s house for a party. In fact, people were shocked that it hadn’t happened before.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Sam and Jess walked into the crowded house, surveying the partygoers for anyone they might know.

 

“Who’d you say was throwing this party again?” Sam asked Jess over the din of music and overly-loud drunken conversation around them.

 

“Some senior – Gabriel, I think. I don’t know him, but everyone was talking about it,” she replied, looking up at him with an innocent smile and batting her eyelashes.

 

Sam raised an eyebrow at her.

 

“Oh c’mon Sam, we haven’t been to a party yet this semester. Let’s live a little,” Jess said with a laugh, standing on her tiptoes to kiss him.

 

Sam rolled his eyes, but his smile betrayed him as he followed her into the throngs of people already adorning the space inside the small house. Sam pulled two beers from the plastic bucket of ice in the living room, twisting the tops off and handing one to Jess. She gave him a peck on the cheek then took a swig from the bottle. Sam led Jess out to the backyard, climbing over a couple entangled with each other and sprawled out on the wooden stairs of the deck. There was a short man with a scraggly beard attempting to make a bonfire in a metal fire pit situated in the middle of the yard. The wind was blowing around them, putting out any lick of flame that began. Sam watched him for a moment as he struggled with lighting the logs and eventually conceded defeat, walking back inside.

 

Sam ended up sitting on a worn wicker bench with Jess on his lap, talking to another guy in his comparative literature class about the assignment that week (until said guy got up to get another drink and didn’t come back, presumably having found something more exciting to do). Sighing, Sam kissed Jess’ shoulder.

 

“You sure you want to stick around, babe? No shame in leaving now.”

 

“ _Yes, Sam,_ ” she giggled, finishing her beer. “I would very much like to stick around.”

 

“Can’t blame me for trying,” Sam chuckled, nuzzling the back of her neck and inhaling the scent of her hair.

 

He was happy, even if he didn’t really want to spend any more time at a party being thrown by a guy he didn’t know. He had an amazing girlfriend and he was at the school of his dreams – nothing could make his life better.

 

“You two look like you could use something more exciting than beer,” a voice said from behind Sam, making him flinch.

 

Jess shifted in his lap, looking up to find the source of the voice. A shorter man with honey-blond hair was leaning on the back of the bench, smiling at them.

 

“So what d’ya say? Want something else to drink?”

 

She nodded, grinning and getting up. “C’mon, Sam.”

 

Sam sighed, shaking his head and following her. The blond man smiled, leading them through the chaos into the much less crowded kitchen. It wasn’t a large room, more a galley kitchen than anything, but it was pretty nice for a college student’s house. The room sported a dark granite countertop with white cabinets above it and stainless steel appliances to boot.

 

“Color me impressed,” Sam whispered to himself.

 

“Hmm?” Jess asked, looking up at him.

 

Sam shrugged. “It’s a nice kitchen is all – more than I’d expect from someone throwing a party like this.”

 

The blond man chuckled quietly and stood on his tiptoes, pulling some bottles out of one of the higher cabinets. He huffed when he couldn’t quite reach a bottle of raspberry vodka on the top shelf.

 

“Mind helping me out, Sasquatch?” he said, looking over at Sam.

 

“Like I’ve never heard that one before,” Sam muttered, rolling his eyes. “My name is Sam,” he added as an afterthought, hoping to avoid more mocking nicknames.

 

Despite his annoyance, he grabbed the bottle with ease and handed it to the shorter man. He nodded once he had the alcohol in his hands, lining up all the bottles on the counter and pulling out some red Solo cups.

 

“Should we really be doing this?” Sam inquired, looking around warily.

 

The shorter man shrugged, starting to pour drinks. He gestured vaguely at Jess then turned towards the counter to pour without spilling booze all over the floor.

 

“And what’s your name, beautiful?”

 

“Jess,” she replied and hoisted herself up on the counter, smiling up at Sam.

 

Sam scowled at the back of the shorter man’s head and watched what he added to the cups carefully.

 

“So what brings two such gorgeous people to a party like this?” he asked, handing them both a plastic cup full of bright pink liquid.

 

Sam blushed at the word gorgeous, filling his mouth with the sickly-sweet alcohol to avoid saying anything stupid.

 

“We wanted a break from the monotony of the dorms, and the quad, and the library, and everything else on campus,” Jess answered with a sigh, taking a sip. “How about you?” Jess continued.

 

“Who doesn’t like a party?” he replied vaguely. “How are your drinks?”

 

“Tastes great. Much better than the beer,” Jess said with a smile, drinking some more. Sam nodded in agreement and leaned against the counter next to Jess.

 

“Not the only thing I have that tastes great,” the other man said, wiggling his eyebrows.

 

Sam turned as pink as his drink again and Jess giggled. The blond man poured them all another drink, stacking the new cups inside the previous ones once everyone had finished their first. He perched himself on a stool across from them, drinking as well.

 

“What does a beautiful lady such as yourself study?” he asked, winking at Jess.

 

“Psychology,” she said with a small smile. “But I’m thinking about minoring in poetry. Well – creative writing with a focus on poetry,” she added with a shrug, but her bright grin made it clear what her passion truly was.

 

“How about you, Tall Dark and Handsome?”

 

Sam grumbled; clearly the guy had a thing for nicknames that he wasn’t about to give up.

 

“Pre-law,” he answered curtly.

 

“Well, you certainly have the personality of a lawyer,” the shorter man commented; Jess laughed and Sam gave her a half-betrayed look because she was supposed to be on his side. “But why would you want to hide a body like that in a stuffy gray suit?”

 

At the rate the conversation was going Sam didn’t think his cheeks would go back to their normal color any time that night. He smoothed the front of his shirt down self-consciously, shrugging a little.

 

“I want to help people,” he filled in helplessly (waiting for the inevitable comment about how he could be a teacher or a police officer or a doctor, certainly not a scummy lawyer, if he really wanted to help people – he was sick of explaining himself to everyone he met – but the comments never came, the shorter man just nodded and gave him a small, genuine smile).

 

“Well _I’m_ studying Theatre and Performance,” the other man said with a grin after the silence settled around Sam’s admission. “Not that I’ve ever gotten cast in any of the productions here,” he continued, scuffing his boot against a rung on the stool and looking down. “But the stage just isn’t ready for the likes of me,” he added quickly, grin falling back into place (but even through the haze of a few drinks it was obvious that his expression wasn’t quite as genuine as it had been before).

 

“So what do you do if you don’t act?” Jess asked.

 

“Mostly backstage work – I’m pretty handy with a spotlight or a soundboard,” he explained, throwing back the rest of his drink. “I’m pretty handy with a lot of things, actually.”

 

He winked and hopped off the stool, turning back towards the counter to pour them all another drink. Jess leaned over and kissed Sam.

 

“Aren’t you glad we stayed?” Jess asked Sam as she took the cup the shorter man offered her.

 

Sam nodded, smiling a little and taking a sip of his fresh drink. The blond man went to the other room with two empty bottles, putting them in the recycling bin. Sam watched him look over the crowd of people in the small house, but he couldn’t see the expression on the other man’s face.

 

“So – who’s this Gabriel guy anyways?” Sam asked conversationally once the other man returned.

 

“That’d be me, kiddo,” the shorter man said with a smug smile.

 

“Oh,” Sam breathed, deliberately not meeting his eyes.

 

“Yeah. Good one,” Gabriel replied, chuckling. “Don’t worry though – I doubt half the people at this party know who I am,” he added, pouring Sam another drink. “And the ones who do don’t actually know me,” he mumbled, too quiet for Sam to hear clearly through the haze of alcohol and embarrassment or over the blur of conversation all around them.

 

“I really shouldn’t-“ Sam said as Gabriel handed him another cup. “My RA can smell beer a block away and this stuff smells ten times stronger – if I drink any more I’m sure he’ll write me up.”

 

“Your loss,” the shorter man shrugged, adding the liquid to his own cup.

 

Jess rested her head on Sam’s shoulder, humming. Sam rubbed his forehead and dropped an absent kiss into Jess’ hair. He nudged her off of him and took her cups from her hands. Sighing, he took them to the trashcan and tossed them in. He turned back and started to ask Jess if she was ready to leave yet, but the words got caught in his throat.

 

Gabriel was kissing Jess.

 

Jess’ arms were slung around Gabe’s shoulders and she certainly didn’t look like she was against the affection. Sam nearly growled, stalking back across the kitchen. His boots clumped loudly against the laminate floor. He was pissed, but he couldn’t ignore the little thrill he felt watching Jess kiss someone else; he pushed that feeling down and focused on being angry. Gabriel pulled himself a few inches away from Jess and craned his head back to look at Sam. He didn’t look apologetic.

 

“What’s wrong, big boy? You want in on this action?”

 

Sam was about to say something (it was going to be sharp and witty, he was sure of it, the alcohol just made his tongue heavy in his mouth) when the shorter man turned to face him and stretched up as tall as he could, pressing a kiss to Sam’s lips. Sam let out a surprised little huff, but he didn’t push Gabe away. The shorter man pulled away and lowered himself down to his normal height again, giving Sam a lopsided smile (and Sam shouldn’t find it cute or charming, but fuck all, he did). Jess giggled, looking between Sam and Gabe.

 

“You have a bedroom we could all use?” she asked Gabriel with a drunken grin.

 

Gabe shook his head, smirking a little as Jess’ smile fell.

 

“If you want a threesome you’re going to have to take a rain check and come back to me in a week. When you’re sober. I’m not gonna be the asshole that ruins your pristine relationship because we all made a decision while drunk that we didn’t like the next morning,” he said, sounding far more sober than he had a few minutes prior. “But don’t get me wrong-“ he continued, looking them both over and giving a low whistle. “I certainly wouldn’t mind being sandwiched between you two.”

 

Sam looked at him, dumbfounded. Gabriel grinned up at him, nudging him towards Jess.

 

“You two get back safe now – go cuddle or do whatever it is perfect couples do. And come back in a week if you want a taste of how great sex can really be,” he quipped as he wrote a phone number on the palm of Sam’s hand then pushed them towards the door.

 

Sam took Jess’ hand and led her back to campus. They didn’t speak over the course of the ten minute walk, both still processing what had just happened (and what exactly they were going to do about it). He checked her in at the front desk of his residence hall, holding her purse for her as she dug through it for her ID card to leave with the desk attendant (an already annoying security measure made more annoying by the alcohol in their systems). They waited for the elevator, Jess not trusting herself to make it up four flights of stairs without hurting herself. Listening to the steady hum and feeling the familiar rumble under his feet let Sam actually think for a moment, rather than letting his mind race as he tried to ignore every thought that poked its way through. There was a too-loud ding as the elevator reached their floor. The doors opened to reveal a deserted hallway. Sam sighed and followed Jess to his dorm room (she knew the way as well as he did, she’d been there so many times). He swiped his ID card clumsily, dropping it in the process.

 

“Fuck,” he muttered, bending down to pick it up off the carpet.

 

“Speaking of – do you think we should take Gabriel up on his offer? Could be interesting…” Jess said, trailing off as Sam stood back up.

 

“We hardly know him, Jess. And we’re still not sober – can we talk about this tomorrow?” he responded, swiping his card again and typing in his code on the keypad (their anniversary, as if he could really choose anything else).

 

She nodded, following him into the room and plopping herself down on Sam’s bed.

 

“Maybe we could get to know him, then?” Jess suggested, doing her best to pull her own jeans off before giving up and flopping onto her back with a huff. “A little help here?”

 

Sam chuckled, helping her out of her clothes.

 

“You want to be his friend? He’s like the most infamous guy at school, Jessica – I doubt he’s friend material.”

 

“We could try,” she pouted, snuggling against his side once he got into bed with her. “He’s funny. You could certainly benefit from lightening up a little.”

 

“Hey,” he murmured without heat. “I’m not as broody as you seem to think I am.”

 

She kissed the underside of his jaw. “Yes, you are – but I love you anyways.”

 

“Let’s get some rest. We have a lot to talk about this week.”

 ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

Gabriel woke up the next morning with a slight headache, sprawled out face down on his bed. He stretched and groaned when some of his joints cracked – he was getting too old to throw raucous parties and flirt unashamedly with tall hotties. He rolled out of bed and padded to the bathroom, looking himself over in the mirror. He shoved a hand through his hair and splashed some water on his face before deciding he looked presentable enough to face anyone who might be sleeping somewhere in his house. He sighed and headed to the kitchen to make some coffee.

 

There were at least a half dozen people scattered throughout his living room, all still asleep. He picked up some of the empty bottles and cups on his way to the kitchen, tossing them into the recycling bin. He turned the coffee maker on and leaned back against the counter, closing his eyes. Chuck walked in, humming to himself.

 

“Did you do anything stupid last night?” Chuck asked, grabbing a box of cereal and a bowl.

  
“Passed up a threesome with Sam Winchester and Jessica Moore.”

 

“Oh wow. And why’d you do that?”

 

“Because they were drunk and I didn’t want to ruin their All-American relationship. I have a heart, y’know,” he said with a dramatic sigh.

 

“You just keep telling yourself that, Gabe. Any chance you might get another offer?” Chuck responded between (and during) bites of cereal.

 

“I told them to come back in a week, sober, if they still wanted to try. I doubt they’ll be back. I cockblocked myself by being too damn responsible.”

 

Chuck clapped him on the shoulder, saying something about how he did the right thing before heading to the living room to kick everyone out. Gabriel chuckled softly at the grumbles of a handful of hungover college kids leaving his house. He poured himself a mug of coffee, emptying three packets of sugar into it before going to sit in the yard to enjoy the crisp fall morning air.

 

He hoped they would come back, but he wouldn’t blame them if they didn’t.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

Jess woke up the next morning with a major hangover. She grumbled and grabbed Sam’s ID card. Putting on one of Sam’s flannel shirts she headed upstairs to use the bathroom, trying her best to ignore the harsh glare of the fluorescent lights above her.

 

Sam woke up when Jess shut the door, rubbing his eyes with a groan. He groped for his phone on the desk next to his bed, checking it for messages. While flicking through unanswered texts (mostly messages from friends who had been just as drunk as him) he noticed the number on his hand. He smiled a little and shot a quick message to Gabriel, just a cheerful good morning as a way of seeing if the older man remembered the night before or if they should all just pretend it didn’t happen at all.

 

 _who is this?_ came the reply a few minutes later. _wait - Sam?_ his phone dinged again before he had even typed a response.

 

 _yeah hey,_ he responded, mentally kicking himself for such a stupid text but smiling when the next reply came even more quickly than the first.

 

 _no way are you sober yet. told you not to talk to me until you’re sober,_ was Gabriel’s response.

 

 _hungover, not drunk. but anyways just wanted to say good morning,_ Sam texted back as Jess came back in.

 

“Who’re you texting? It’s like 10 AM on a Sunday. Who the hell is even awake?” she grumbled, crawling back into bed with him and burying her face in the crook of his neck.

 

“Gabriel.”

 

“Well tell him I say hi. Wake me when it gets dark again. The lights are hurting my head,” she mumbled with a pout Sam could practically feel.

 

Sam chuckled, kissing her hair. Hesettled back down, slinging an arm over the curve of her waist. She sighed and dozed off quickly. Sam put his phone back on his desk and joined Jess in dreamland.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

The week passed quickly, a blur of classes, worry and a hefty dose of uncertainty. Sam and Jess danced around the subject of Gabriel with each other, both unsure of how far to push the other in terms of making a decision. Something needed to give.

 

“We should talk about this,” Jess suggested while they were waiting in line in the cafeteria to get some lunch.

 

“About what?” Sam asked absently as he put together a salad from the salad bar, considering tomatoes before deciding against them.

 

“About Gabriel. Even if we decide not to do anything with him, we at least have to go tell him that face-to-face. It would be rude to leave him hanging. So we have to talk and figure out what we’re doing and what we’re going to tell him,” she said, handing her school ID to the cashier and paying for her food.

 

“Okay. Well what do you think we should do?” he asked as they sat down at a secluded table by the window, hoping for a little privacy to talk.

 

“I liked him. He was funny and kind and a pretty good kisser,” she said, smirking when Sam grumbled at the last part. “Shut up, you thought so too. But I don’t just want to have an awkward threesome with him – those are hard when you’re not drunk and he’s clearly pretty set on not drinking and fucking, at least the first time around.”

 

“So what are you suggesting?”

 

“Maybe we could try to be his friend. And maybe something more will come of it.”

 

“Polygamy, Jessica?”

 

“Well, sort of. I guess it would technically be polyamory because we’re not married,” she said with a shrug.

 

“You’ve looked into it,” Sam replied, raising an eyebrow in amusement.

 

“A little. Don’t be an asshole. Anyways, we don’t have to do anything at all if you don’t want to, but I think it would be interesting to try. And he likes us both, Sam. And you definitely seemed to like him.”

 

He paused, chewing his salad thoughtfully before nodding. “Sure, we can try it.”

 

Jess grinned, kissing Sam’s cheek. With a tentative smile he got up to throw away his trash.

 

“Let’s go see him today then – I’ll text him and see when he’s free.”

 

They walked outside, Sam texting Gabriel. He kissed Jess before heading off to his next class, stashing his phone in his bag. He sat through an hour of class on the edge of his seat, ready to grab his phone and check for a response the second the class ended. When it finally did, after what felt like too long, he yanked his phone out of his bag and checked for texts. There was one from Gabriel.

 

_sure you guys can come over today kiddo. 5 sound good to you?_

 

Sam sighed at the nickname, but he found that he kind of liked it (though he wouldn’t admit that to Gabriel or Jess any time soon). He shot back a quick reply to tell Gabe that they would be over around 5 then went to find Jess. He called her cell. Her roommate, Ruby, picked up.

 

“Hey there,” she said with a chuckle. “Your perfect girlfriend is in the shower, can I take a message? Or maybe I can just take you.”

 

Sam rolled his eyes. “Just tell her to meet me by the library at 4:30, Ruby.”

 

“Sure thing, sugar,” she answered sarcastically, hanging up without saying goodbye.

 

Ruby was true to her word, however, because Jess met Sam outside the library at promptly 4:30.

 

“You nervous?” she asked, taking his hand.

 

“A little. I don’t know. I’m not sure what to expect.”

 

“I understand. I guess we’ll just see when we get there,” she replied, leaning up to kiss his cheek.

 

He nodded; they walked the rest of the way in silence, both swimming in their own thoughts about what they were getting themselves into. They got to Gabe’s house, getting a little lost in the process of trying to find it during the day rather than at night like last time. Sam sighed and rang the doorbell, squeezing Jess’ hand and waiting for someone to answer. A short man (even shorter than Gabriel) answered the door. Sam frowned.

 

“Is Gabriel here?” he asked.

 

“Huh. Oh yeah, he is. C’mon in,” he responded quickly, opening the door all the way to let them in. “I’m Chuck, by the way. I’m Gabe’s housemate – I’m mostly just here to do the dishes though,” he continued with a genial expression that said he’d been living with Gabriel’s antics for a while and was used to them now.

 

“Hey, I heard that. Don’t scare them away before I even get to talk to them, Chucky,” Gabe yelled from down the hall.

 

Jess chuckled, bending down to pet the dog that trotted up to see them.

 

“Who’s this cutie?” she asked, looking up at Chuck as she scratched behind the Jack Russell Terrier’s ears.

 

“That’s Tiny. He’s Gabe’s,” Chuck responded with a smile, heading down the hall to his room to give them some privacy.

 

Gabe came out of his room just as Chuck’s door closed, smiling at them.

 

“Well well well, did you decide to cash in your rain check?” Gabe asked with a cocky smirk.

 

“Not exactly. We want to talk first,” Jess said with a smile, standing up to her full height again.

 

Gabe’s smirk faltered slightly and he nodded. He led them to sit down at the kitchen table, quickly moving the dirty dishes to the sink.

 

“Sorry about the mess,” he muttered, trying to sound nonchalant, but his blush gave him away as actually being embarrassed.

 

“Don’t worry,” Jess said gently, smiling.

 

“So… talking,” Gabe huffed nervously, tapping his foot.

 

Sam put a hand on Gabriel’s shoulder, smiling. “Calm down, Gabe. It’s just talking.”

 

“Sex would be easier.”

 

“We don’t just want to have a meaningless threesome with you, Gabe. We’d like to get to know you better,” Jess started, jumping right into it to nip any more nervousness in the bud. “We’d like to be your friends and maybe, if it happens to go that way, to be something more.”

 

Gabe nodded a little. It was obvious by the way he was looking at them that it wasn’t what he was expecting.

 

“You want to be friends?”

 

“And maybe something more, if it happens,” Sam repeated, reminding Gabriel of the second part of Jess’ offer. “Look – we think you’re someone worth spending time with is all we’re saying. We don’t want our only interaction with you to be fucking. But it’s up to you at this point.”

 

“Okay. Yeah, okay, we can try that,” Gabriel nodded slowly, a small smile forming on his face. “I think I’d like that.”

 

Jess smiled. “Maybe to start it off you could show us around your house?” she offered. She hoped something simple would help Gabe get more comfortable with the idea.

 

He nodded, getting up and offering them both a hand. Jess smirked and took it, standing up with him. Sam looked a little more apprehensive, but he eventually followed Jess’ lead and followed Gabe on a tour of his house.

 

It wasn’t large, but it was certainly far bigger than the dorms that Sam and Jess were used to. There were two bedrooms, the neater and less opulent one occupied by Chuck and the messier but more hedonistic (did a single college student really need a king bed, Sam found himself wondering) one belonging to Gabriel. He apologized for the mess again, but Jess shushed him and gave him a kiss on the cheek, telling him just to continue with the tour. Next up was the bathroom, then the living room with only a couch, an arm chair, a television and a bookshelf, and finally back to the kitchen.

 

“So – that’s it,” Gabriel shrugged.

 

“It’s very nice,” Jess smiled and looked up at Sam. “Maybe we could all go out for coffee later this week – see where that gets us?”

 

Sam and Gabriel both nodded. Jess smiled, kissing Sam’s cheek. Gabriel showed them out, smiling a little.

 

“So – what’s the deal with them?” Chuck asked, coming out of his room in time to see Sam and Jess walking down the driveway.

 

“I,” he paused, pushing his hair out of his face with a sigh. “-think they want to date me. Well, not right away, but… I think they want to date me, not just fuck me,” Gabriel said, sounding a little dumbfounded.

 

“Really? That’d be your first real relationship since – well since Kali, right?”

 

“Shut up.”

 

“Touchy subject? I thought you and Kali were still friends, man.”

 

“We are. I just don’t wanna think about how long it’s been since I had a relationship that lasted more than one night,” he sighed, mumbling. “I’m worried I’ll fuck this one up.”

 

Chuck shrugged. “Do you think it’s worth the risk of screwing up to have the chance at a relationship?”

 

Gabriel paused to think for a second, looking at the ground. “Yeah. Yeah, I think so.”

 

“Then go for it. The worst that can happen is that nothing comes of it.”

 

Gabriel nodded slightly, sighing. Chuck was right, the worst that could happen didn’t sound so bad; it would be worth it.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

After some texts back and forth and some maneuvering of schedules they finally settled on an afternoon to have coffee all together. Sam and Jess met at the café after class and waited for Gabriel. There was hardly anyone there, just another college student in the corner working on his laptop and the employees; it was fairly quiet for a Friday afternoon. Sam sighed; Jess bumped her knee gently against his.

 

“Nervous again?”

 

“A little. It’s like a first date, I guess. I sort of hate first dates. They’re always awkward.”

 

“Just think of it as coffee with a friend. That’s all it really is, anyways. We’re not dating him yet, Sam.”

 

The bell over the door jingled and Gabriel walked in. Smiling, Jess gave him a little wave.

 

“Hey. How are you?”

 

“Fine. How are you guys?” he replied with a shrug, sitting with them after getting some coffee.

 

They continued in the vein of friendly small talk, nothing of consequence until Gabe sighed and looked down at his coffee.

 

“Sorry if I’m a little – bad at this. The last time I dated was… shit, back in high school. And I wouldn’t even really call it dating, it was more being ordered around by my girlfriend, Kali. She’s great, we’re still friends and all but,” he paused when he realized he was starting to ramble. “But I haven’t dated in a _long_ time, is basically all I’m saying. Sorry.”

 

Jess smiled, putting her hand on top of Gabe’s. “It’s okay. You’re doing fine, y’know. Don’t worry.”

 

He smiled a little, turning his hand over and taking hold of Jess’. Sam tried to keep his jealousy in check, but he couldn’t help the little grumble he let out seeing Jess be so affectionate to someone they hardly knew. She smiled, taking Sam’s hand with her free one.

 

“Calm down, Sam. You sound like a territorial caveman when you do that,” she chuckled, squeezing his hand.

 

Sam blushed, looking away for a second. Gabriel smiled and put his free hand on Sam’s cheek to turn him back to look at them.

 

“I think the territorial caveman act is kinda hot,” he said, smiling genuinely.

 

Turning back to look at them, Sam snorted out a laugh. “Thanks, I guess.”

 

“Any time, sexy,” he responded, pulling his hand back before Sam had a chance to react.

 

They all had another cup of coffee, sharing a few pastries between them (Gabriel definitely had the biggest share, though Sam and Jess didn’t mind). Before they knew it the sun was setting. Sam checked his phone.

 

“Fuck. I have a paper due by midnight and I haven’t really started yet,” Sam muttered after he checked the time. “I should go work on it,” he said without much conviction, looking between Jess and Gabe.

 

They nodded and all three got up, heading outside.

 

“This was really nice. Maybe we could do something like this again soon?” Gabriel asked, nervously scuffing his boot against the pavement.

 

“Sure. That sounds great,” Jess answered as Sam nodded. “Text us, we’ll make some plans,” she continued, leaning down to kiss his cheek.

 

Gabriel looked unsure of what to do until Sam followed Jess’ lead and kissed Gabe’s other cheek.

 

“We’ll see you around, Gabriel,” Sam said, leading Jess back to campus.

 

He smiled, touching his cheeks briefly before heading back home, feeling happier than he had in a while. Tiny greeted him at the door, Chuck waving from the couch where he was watching television.

 

“How was it?” he asked, muting the show he was watching.

 

“Good, actually. I mean – I don’t really remember how to date people, but they seemed pretty happy with what I managed to do. And they asked me out again.”

 

“You think you’re going to take them up on that offer?”

 

Gabriel nodded, pushing a hand through his hair nervously.

 

“I just – god, I want them to _like_ me. I feel like I’m in high school again, trying to court Kali. But I think I might actually have a chance to have something real with Jess and Sam. I feel like I’m fifteen again and it’s not exactly an age I want to relive,” he sighed, shaking his head.

 

“Yeah, you were pretty gross then,” Chuck commented, chuckling.

 

“Look who’s talking, Mr. Headgear,” Gabriel sniped back, glaring.

 

“Hey, I was kidding. Mostly. Don’t be an asshole, Gabe. Besides, you can’t deny you spent most of that year following Kali around like a lost puppy. It _was_ pretty gross.”

 

“Fine. Shut up. I just want this to work out.”

 

“Any help you need, man, I’m here for you.”

 

“For starters, what’s a good second date?”

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

Taking Chuck’s advice, Gabriel took Sam and Jess bowling the next weekend.

 

“It’s not much, but I thought it could be fun,” Gabriel said, looking like he regretted listening to Chuck the second they walked into the bowling alley.

 

Jess grinned, taking both of their hands and leading them to get bowling shoes.

 

“I haven’t been bowling in years,” she said, pulling her shoes on. “Don’t laugh if I suck at it.”

 

Sam chuckled, getting his own shoes on. “Don’t worry, no matter how bad you are, I’m sure I’m worse.”

 

Gabriel raised an eyebrow at Sam’s shoes; Sam gave him a look. “Can I help you?”

 

“You know what they say about a man with big feet, don’t you?”

 

Sam rolled his eyes; Jess laughed.

 

“If it’s what I’m thinking of, they’d be right,” Jess said, still giggling.

 

“Hey,” Sam muttered.

 

“It’s not a bad thing, Sammy,” Gabriel said, winking. “In fact, it’s a great thing. I like ‘em big.”

 

Jess got up and put herself between them before they could say anything else.

 

“Time to go bowling, you two. Don’t kill each other before we finish the game.”

 

They followed her to the lane, all inputting their names into the scoreboard. Jess took the first turn, scoring a strike right off the bat. She squeaked and did a little spin before blushing when she realized how silly she must look.

 

“You’re cute,” Sam said, kissing her cheek as she came to sit down.

 

Gabe went next, managing to knock down eight pins in total; he shrugged and sat back down as Sam got up. He knocked down all of two pins over the course of his turn, hanging his head in mock-shame as he sat back down. Gabriel laughed and kissed his cheek.

 

“It’s just a game, kiddo. Don’t worry.”

 

Sam smiled a little at the affection, taking Gabe’s hand loosely when he offered it. He absently rubbed Gabe’s knuckles with his thumb as Jess took her next turn; Gabriel turned a little pink, smiling.

 

They got pizza halfway through the round, laughing and dancing around each other as they all tried to eat and take their turns without running in to the others. Gabriel managed to almost break Sam’s bones with a bowling ball, accidentally throwing it backwards during his last turn – it landed only a few inches from Sam’s right foot. Gabriel looked horrified; Sam just laughed.

 

“What, are you trying to get me out of the way so you can have Jess?” he said teasingly.

 

“Maybe,” Gabe replied in the same tone as Sam. “But I’d really like to get you naked at least once before I get rid of you.”

 

Before he turned to finish off his round he saw that Sam blushed. Gabe grinned triumphantly and finished his turn (deliberately shaking his ass as he rolled the ball down the lane). Sam took his last turn after Gabe, passing by him to go pick up a ball. Gabriel grabbed his ass as he went by, then went to sit with Jess innocently.

 

“Watch it,” Sam grumbled, taking his turn.

 

“I plan on it,” Gabe replied, eyeing him up and down as he bowled his last set.

 

Jess won by a landslide, followed by Gabe and finally by Sam who lost pretty badly. Jess and Gabe only teased him a little on their way back, much to his relief.

 

“I had a great time. Thanks,” Gabe said once they got back to the school.

 

He leaned up and kissed them both on the lips briefly. “Maybe we could do something again next weekend.”

 

“Sounds perfect,” Jess replied with a smile.

 

“We had a great time too,” Sam chimed in. “It was nice to get a break from studying. And it was nice to spend more time with you,” he continued, taking Jess’ hand. “We’ll see you around.”

 

Gabriel couldn’t stop smiling the whole way back to his house from campus.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

“You took them _bowling_ , Gabriel? I sincerely hope this is you trying to be funny after not calling me for weeks,” Kali sighed exasperatedly.

 

“I – is it really that bad? They had fun. At least I think I did. Fuck – did I just ruin everything?” Gabe said, speaking quickly.

 

“Calm down. If they seemed to like it, they probably liked it. I just can’t believe you actually took those two bowling. I saw the picture you sent me – they’re rather out of your league. I thought you would have tried for something… classier,” she said, resting her phone between her ear and her shoulder as she put away her textbook.

 

“Hey, not all of us have fancy well-paid internships, princess,” he grumbled back. “And I know they’re out of my league, that’s why I called you. I need help. What’s a good idea for another date?”

 

“Try something from the heart. Make them dinner at your place, perhaps?”

 

“I’m not much of a cook,” Gabe said, rubbing his forehead. “I think that would just scare them off, not make them want to actually date me.”

 

“I’m sure you could manage _something._ I think they’d appreciate a home cooked meal of any sort, Gabriel. They do live in dorms and eat in a school cafeteria. As for your second point – well, it sounds as if you’re already dating them.”

 

“Fine. I’ll try it. But if it crashes and burns it’s all on you, Kali,” he mumbled, looking through the cabinets in the kitchen. “I’m gonna need to go grocery shopping. We pretty much only have cereal and ice cream.”

 

“Sounds just like you and Chuck, I’m not surprised,” she scoffed. “Just – try to do something nice and thoughtful for them, I think it will impress them more than you think.”

 

“Okay,” Gabe sighed. “Thanks for the advice, Kali. You’re a lifesaver and I love you. Or if this doesn’t work, you ruined everything and I hate you.”

 

“Don’t be so dramatic, Gabriel. And call me more often. I want to hear how it goes.”

 

“I’ll keep you updated. Bye,” he said as he hit “end call”, sighing at his empty cabinets.

 

Shooting off a quick text to Sam and Jess inviting them over for dinner the next weekend, he dragged Chuck to Safeway. It hit him on the way over what Kali had said – “it sounds as if you’re dating them already”. He swallowed hard as they walked in the automatic doors and grabbed a cart. He wasn’t going to think about it because he didn’t want to assume what it was that they had, he just wanted to have it.

 

“What should I make? Fuck. What the fuck should I make?” he said mostly to himself, rushing through the aisles and almost crashing into a display of Fruity Pebbles.

 

He ended up grabbing the makings for lasagna, enough to make about twenty because he panicked. They got back to the house and Gabriel set about trying to make a lasagna just to see how hard it would be; he had settled on it because he thought it would be easy. He was wrong. The first one came out burned worse than Gabe thought it was possible to burn food. He offered it to Chuck who raised an eyebrow and told him that he had better practice.

 

“Shit.”

 

He spent practically every free moment during the week practicing making lasagna and making Chuck try every (edible) failed attempt. By the time Saturday rolled around Gabriel was sick of making lasagna (and Chuck was sick of eating it), but the results of his last few attempts were clearly a lot better than his first. He hoped Sam and Jess would enjoy it, or at least pretend to for the sake of his pride.

 

He was still scurrying around the kitchen trying to finish dinner when the doorbell rang.

 

“Shit,” he mumbled, turning on the timer and going to get the door.

 

Sam and Jess smiled at him when he opened the door, Jess holding a bottle of wine. Gabriel smiled a little and let them in before dashing back to the kitchen to make sure nothing burned.

 

“Make yourselves at home. By the way, how did you buy that wine? You don’t look the types to have fakes,” he called over his shoulder, pulling the lasagna out of the oven and sighing in relief when it actually looked presentable.

 

“My roommate, Ruby, has one. Had her buy it. She owed me a favor anyways,” Jess said as she came out to join him in the kitchen, putting the wine on the counter. “Need any help?” she asked, smiling.

 

“You really don’t have to – there’s not much left to do anyways.”

 

“I want to. It’s not like I get to cook at school at all – I miss it.”

 

Gabe nodded. “Okay. Thank you. Maybe you could get the garlic bread out?” he asked, turning towards the lasagna to cut it.

 

Jess smiled, humming as she took the pan out of the oven and placed it on the counter.

 

“How has your week been?” she asked as she washed her hands.

 

“Uh – saucy,” he responded, smirking a little. “I made… well, I’m not gonna lie, I made a lot of lasagna. I’m not really much of a cook, so I had to practice,” he continued, turning a little pink. “Sorry if it’s still not that good. I tried.”

 

“I’m sure it’ll be wonderful. Sam and I don’t have a lot to compare it to, we have to eat cafeteria food most of the time. Don’t worry, we’re going to be impressed,” she said, kissing his cheek. “Besides, _you_ made it – that’s enough for us.”

 

Gabe turned away so Jess wouldn’t see his embarrassingly large grin. “Shoo now. Go sit at the table with Sam so I can properly wine and dine you two.”

 

She giggled, going to get Sam and sitting at the table with him. Gabe started with the wine, bringing out three long-stemmed glasses and pouring them all some of the illegal red that Jess had gotten. Jess could tell starting with alcohol was deliberate – Gabriel seemed ten times calmer with a little wine in him. They discussed their weeks, Sam lamenting about his philosophy teacher who insisted on assigning hundreds of pages of reading a week.

 

“It’s a gen ed class,” he pouted, also calmer and looser with some alcohol in his stomach. “No one else even fucking does the reading, but I’d feel bad if I didn’t.”

 

“Wow, you really are a nerd,” Gabe laughed, leaning over to kiss him firmly on the lips. “Nerds are the new sexy or something, right?”

 

Sam chuckled nervously, licking his lips and tasting wine and Gabriel. Jess smiled; she was glad they were letting themselves go around the other (especially Sam towards Gabe – Gabe was comfortable in his own sexuality from the get-go, it seemed). She knew Sam had years and years of bigotry shoved down his throat by his father – it could make anyone, even someone as strong as Sam, have at least some internalized homophobia. When Sam leaned in and initiated the next kiss, fisting his hand in the fabric of Gabe’s shirt, Jess cleared her throat.

 

“How about dinner first? Then if you want to make out, you two can certainly make out. Though I’d like to be involved too, y’know,” she said playfully.

 

Gabe grinned, leaning over and kissing her just as much as he had kissed Sam. “You sure you want dinner first?”

 

“ _Yes,_ ” she answered. “Please – I’m starving.”

 

“Okay, okay, dinner first,” Gabe laughed, getting up and heading back to the kitchen.

 

He brought out the lasagna and garlic bread, pouring more wine for them all. Once Gabe sat back down with them they all started eating.

 

“This is really good,” Sam said while he ate. “Thanks for having us over.”

 

Gabe smiled, eating his own dinner. They ate mostly in silence, enjoying each other’s company and the food. They drank enough to feel pleasantly relaxed; Gabriel cut them off before anyone got inebriated because he ‘still wanted a chance to get a little more familiar with them without alcohol clouding anyone’s judgment’. He winked at them after that, getting everyone a glass of water instead. After everyone finished eating Gabriel smiled at them and cleared the table. Jess and Sam followed him into the kitchen.

 

“We can help clean up,” Sam offered.

 

Gabe looked up at them, smiling. “Sure – sounds domestic.”

 

Sam raised an eyebrow.

 

“Hey, domestic isn’t a bad thing. In fact, I think domestic is something I’d really like.”

 

“Yeah?” Jess asked, sliding in next to him to wash the dishes.

 

“Yeah. I guess… well, I guess domestic isn’t something I’ve ever had. My childhood was kinda strange, I’m not gonna get into that right now, and I was basically kicked out when I left for school. And Chuck and I aren’t exactly domestic together, we’re just two messes on top of each other making an even bigger mess,” he said, smirking a little.

 

Sam kissed his cheek and took the clean dishes from Jess to dry, handing them to Gabe to put away.

 

“We can do domestic,” Sam said. “If that’s what you want, that is.”

 

Gabe nodded slowly, looking between the two taller people on either side of him. He was a little shocked that two people this amazing were willing to stick around with him even after bowling and a badly home cooked meal.

 

“Really?” he asked as he put away the dishes.

 

“Yeah. We’re willing to do that, right Jess?”

 

Jess nodded. “Domestic sounds really nice.”

 

Gabriel grinned and took their hands once all the dishes were put away, leading them to the couch.

 

“So, about that whole making out thing – is that still something you two want to do?” he asked softly, irrationally afraid that if he got too excited they would find something better to do than spend time with him.

 

Sam smiled, leaning over and kissing Gabe soundly on the lips. Gabe melted into the kiss. He wrapped his arms around Sam’s shoulders, a sound like a purr coming from his lips when Sam pulled back enough to breathe.

 

“Is that a good enough answer for you?”

 

Gabe nodded dumbly, leaning back in to kiss him again. Jess cleared her throat. Sam pulled back from the kiss. He nudged Gabe towards Jess. The smaller man eagerly turned to face Jess. She pulled him in for a kiss and gestured for Sam to come closer to them. He settled behind Gabriel, awkwardly placing his hands on either side of Gabe. Gabe chuckled against Jess’ lips and pulled away.

 

“No need to be so formal,” he murmured, taking Sam’s hands and placing them on his hips.

 

He leaned back against Sam a little, hoping the larger man would get the picture. Sam huffed a little, but he leaned down to kiss along Gabe’s neck as Jess went back to kissing his lips.

 

“A guy could get used to this,” he sighed happily the next time he pulled away for a breath. “Maybe we could do a little more, if you catch my drift.”

 

When neither Jess nor Sam did anything more he slid back a little further, practically sitting in Sam’s lap.

 

“Is that a no?”

 

“I think it’s more that we don’t really know what to do when there are three people…” Jess supplied, looking back at Sam who nodded in agreement.

 

Gabe smirked.

 

“I can help with that. Believe me, this ain’t my first rodeo,” he said, then paused. “But it might be the first where I’ve known everyone else’s name,” he chuckled dryly, hoping to convey that he was (mostly) kidding.

 

He shook his head and sighed, taking one of Sam’s hand and put it over his crotch.

 

“You ever been with another guy, kiddo?” he asked with his head tilted back to see Sam’s face.

 

“No. No, I haven’t,” he responded with a nervous tinge to his voice.

 

“Don’t worry, big boy, it’ll be okay,” Gabe said, leaning up to kiss Sam’s jaw. “We don’t have to do anything you’re not comfortable with. And if you’re not sure what to do then when you’re touching me just pretend you’re touching yourself – might help you get a grip on it,” he finished with an encouraging smile.

 

Sam huffed out a laugh at the double entendre, rubbing Gabe through his jeans. “Like this?”

 

Gabe sighed happily and pushed his hips up against Sam’s hand.

 

“Perfect. Keep going.”

 

Jess smiled and kissed Gabe.

 

“Is it okay if I touch you, beautiful?” Gabe asked Jess.

 

She nodded, smiling. He slid his hands up her sides, cupping her breasts. Wiggling his hips in Sam’s lap a little to tease him, Gabe brushed his thumbs over Jess’ nipples through the fabric of her shirt and bra.

 

“Maybe we could get some clothes out of the way,” Gabe suggested as he leaned up to kiss the underside of Sam’s jaw.

 

“Maybe we could take this to the bedroom before we do that,” Jess countered, getting up.

 

Gabe grinned and followed her lead, Sam following them both back to Gabe’s bedroom.

 

“Is this why you have a king bed?” Sam asked with a smirk. “To accommodate threesomes?”

 

“Don’t limit me like that – I like ‘somes of every size,” Gabe responded, laughing. “I’m a hedonist at heart, what can I say? I like nice things and I like them big. Why do you think I’m so attracted to you two? Nice, tall, and beautiful – you two are the whole package.”

 

Gabe nudged them both to sit on his bed, positioning himself in front of them. Finally past the awkward small talk, Gabe felt more in his element. Cocky during sex he could do; it was stuff outside the bedroom that scared him.

 

“You two just sit back and enjoy the show,” he said with a sly smile as he started to unbutton his shirt.

 

Sam raised an eyebrow, but he didn’t look away. Jess giggled, just enough wine in her system to make her bubbly. Gabe performed a full striptease for the two of them, whistling a tune that reminded Sam of something Dean would listen to (he thought the group name might be a state or a country or something like that, but in the heat of the moment he couldn’t quite put his finger on it). Gabe wiggled his ass in their direction and snapped Sam out of his thoughts.

 

“C’mon, I’m not gonna be the only naked one here,” Gabe pouted. “Wouldn’t be much of a threesome if that was the case.”

 

Jess gracefully got undressed; she put on less of a show than Gabe did, but she looked beautiful doing it. Sam kicked his jeans off as he watched her, sneaking glances at Gabriel every so often. Jess walked over to where Sam was still sitting on the edge of the bed, bending down to reach his shirt and unbuttoning it for him. He wouldn’t admit it if someone asked him, but he definitely wasn’t looking at her face while she was taking his shirt off for him.

 

“I love you,” Sam said, looking up at Jess.

 

“I love you too,” she replied, kissing him.

 

Gabe cleared his throat awkward, rocking back and forth.

 

“I can go…”

 

“Sorry,” Jess said, pulling away from Sam. “Like I said, we don’t really know what to do with three people. Mind giving us some direction?”

 

“I could,” he smirked. “For future reference, I usually like to be the one who gets directions. I like to be spanked too,” he continued, laughing as he got on the bed with them.

 

Gabe leaned in to kiss Jess first. His hands danced across her skin, teasing and touching on the quest for erogenous zones. He kissed down her neck and chest, nudging her to lay down on her back. She smiled up at them as Gabe turned to kiss Sam.

 

“I was thinking we could show this lovely lady a good time before we got to anything too – well, penetrating.”

 

Sam raised an eyebrow, but nodded just the same. Jess grinned.

  
“Sam’s awful good at putting his money where his mouth is,” she said, happily spreading her legs for them.

 

“Tongue of gold against your soul says I’m better than you, Sammy,” Gabe chuckled as he settled between Jess’ legs.

 

Sam wrinkled his nose at the nickname, but he joined Gabriel between Jess’ legs anyways.

 

“This is going to take some getting used to,” Sam muttered, trying to fit his limbs in next to Gabriel’s without hurting Jess.

 

“But once we do get used to it, it’s gonna be awesome,” Gabe responded, kissing Jess’ thighs.

 

Jess purred, petting Gabe’s hair with one hand. Sam leaned in and nuzzled her hips, earning himself Jess’ free hand in his hair.

 

“Can’t wait to feel what you guys can do,” she sighed happily, closing her eyes.

 

Gabe kissed his way up her thighs, smiling between each kiss. He winked at Sam and began peppering kisses over her slit. She squeaked softly, then relaxed.

 

“Oh,” she murmured as Gabe used his thumbs to spread her open more.

 

Sam joined him and tentatively leaned in to kiss her folds alongside Gabe. It was a tight fit with both of them down there together, but if Sam had learned anything in his time with Jess it was that she was flexible and enthusiastic. She spread her legs even further to accommodate them, petting their hair while they continued kissing her.

 

“I could die happy,” she purred, tugging Gabe’s hair a little when he flicked her clit with his tongue. “Shit, sorry.”

 

He lifted his head a little to speak, letting Sam take over for a moment.

 

“Don’t apologize, I liked it.”

 

She opened her eyes a little, grinning down at him.

 

“Yeah?”

 

He just nodded in response, dipping his head back down to join Sam again. They continued kissing and licking her, working her until she was moaning louder with each touch of tongue and lips to her.

 

“Hey, kiddo – want to try something really fun?”

 

He nodded; he was still wary of Gabe, but his ideas hadn’t been bad up until that point so he was willing to give him the benefit of the doubt and go with him on this one. Gabriel grinned, wrapping an arm around Sam’s shoulders and pulling him closer to himself and Jess. He kept Sam as close as he could manage without hurting someone and kissed him. They kissed sloppily, keeping as close to Jess as possible so their lips and tongues brushed against her clit with every movement. Jess peeked down at them to see what was going on and immediately tightened her grip on their hair.

 

“Fuck – you guys look so hot like that,” she said, worrying her bottom lip.

 

Gabe pulled away from Sam, leaving him a little dazed. The shorter man purred and circled Jess’ clit with his lips, sucking happily. She whimpered and almost shut her thighs around Gabe’s head in surprise.

 

“Shit,” she whined, panting softly. “You’re really are good at this.”

 

He chuckled, sending pleasant vibrations through Jess and making her moan even louder. Sam fitting himself in and pressing his tongue inside her sent her over the edge with a squeal. They coaxed her through it then pulled back. Gabe pulled Sam in for another kiss and smiled.

 

“See, wasn’t that fun?”

 

Sam didn’t answer, instead just continuing to kiss him. Jess finally caught her breath and sat up a little.

 

“You two are amazing.”

 

“Who’s better?” Gabe asked with a smirk in between kisses with Sam.

 

“You’re both good. I don’t know if I can ever go back to only having one person at a time do that for me though – that was incredible. What can I do for you two?”

 

Gabe smiled and stretched over the side of the bed, rummaging around in the drawer of the bedside table.

 

“Well, I was thinking…” he began, making a victorious noise and holding up two condoms. “That we could try something along the lines of you riding me while Sam fucks me. Figured it’d be easiest,” he finished with a shrug.

 

Sam and Jess glanced at each other and nodded.

 

“That sounds good,” Jess said.

 

Gabe smiled, settling on his back in the middle of the bed. He ripped open one of the condoms and handed the other to Sam. Gabe rolled his on to his cock with practiced ease, reaching for Sam after he finished. He pressed a tube of lube into Sam’s palm.

 

“You know what to do with this, big boy?”

 

Sam nodded a little, looking at the unassuming container in his hand.

 

“Maybe I should prep myself and walk you through it this time? I can promise you’ll like the view,” he said cockily, taking the lube back from Sam.

 

Sam nodded and sat back on his heels to watch Gabriel. Gabe winked at him again, flicking the lube open and spreading some on his index and middle finger. After a quick look down at Sam’s cock he added his ring finger to the mix as well.

 

“Gotta say, Sam – you might be the biggest I’ve ever seen. And I’ve seen a lot.”

 

Sam blushed, but he didn’t look away. Gabe smiled and spread his own legs, letting his hand drop down between them. He rubbed his hole briefly with the tips of his lubed fingers before carefully pressing his index finger in.

 

“Fuck,” he mumbled, biting his lip as he gave himself a second to relax before pushing the finger all the way in. “You watching this, Sam?”

 

Sam nodded dumbly, transfixed by Gabriel. Jess settled next to Sam, watching Gabe put on his second show of the night for them. He lost his cocky veneer while prepping himself; he was hardly able to talk Sam through it, too caught up in the feeling of his own fingers inside him. Once he was stretched wide around three fingers he drew them out of himself and looked up at Sam.

 

“I’m all ready for you now, kiddo,” he said, grabbing a tissue to wipe his fingers clean with.

 

Sam quickly put on his own condom and settled between Gabe’s legs.

 

“You look really incredible like this,” he said reverently, rubbing Gabe’s thighs as he looked him over.

 

Gabe’s cock curved up towards his stomach more than his own did and Sam found he couldn’t help but wrap a hand around it and stroke a few times, just to see how it felt. Gabe’s whine brought him back to his senses and made him drop his hand back to his thigh.

 

“Sorry.”

 

“Oh, I definitely wasn’t complaining, Sammy. Just don’t want this to end too soon. And with the way your hand feels on my cock – well, I definitely wouldn’t last long like that.”

 

Sam let out a short, exasperated laugh and bent down to kiss him, lifting one hand to Gabe’s chest to feel his way down the other man’s torso. It was a new experience for him; Gabriel wasn’t particularly muscular, but he wasn’t exactly as soft and curvy as the girls Sam had touched before were either. He was something new entirely and Sam found that he liked it a lot.

 

“So are you gonna get that big cock inside me any time soon or should I flip us and just ride you to speed up the process?” Gabe asked, looking up at Sam.

 

“Sorry, just – I like touching people a little before I fuck them. Makes it feel more real, I guess. That probably sounds dumb, sorry,” he muttered, looking down at the sheets.

 

“Hey. That doesn’t sound stupid, it sounds sweet. And I _really_ like sweet – usually in the form of candy, but a gorgeous guy like yourself could satisfy my craving just as well as any sugar.”

 

Sam found himself blushing again, still absently touching Gabe’s chest and stomach.

 

“C’mon now. I wasn’t kidding, Sam – I am dying to have you inside of me. Grant me that at least?” he asked, smiling.

 

Sam straightened up again, lining himself up with Gabe’s hole and pushing in slowly. He kept an eye on Gabe as he pushed in, watching for any signs of discomfort, but all he saw was Gabriel slack-jawed and purring.

 

“That feel good?” Sam asked as he finally bottomed out and paused to adjust to the feeling.

 

“You have no idea, kiddo,” Gabe replied hazily, already thanking whatever gods there were for Sam Winchester and his huge dick.

 

After a minute of feeling Gabe relax around him enough to facilitate some actual movement, Sam nudged Jess.

 

“Maybe it’s time you joined us,” he said, looking at Gabriel who just nodded lazily.

 

Jess smiled and straddled Gabe’s hips before sinking down on his cock. Gabriel rested his hands on Jess’ hips, tracing the bones with his thumbs. He smiled up at her.

 

“You really are gorgeous,” he said.

 

She leaned down to kiss him, smiling.

 

“Thank you. You’re not so bad yourself,” she responded after the kiss.

 

Sam found he wasn’t quite sure what to do with his hands in this position. He settled for rubbing Gabe’s thighs because they were just about the only thing he could reach without jostling Jess. He jumped a little when something touched his hand; it was Gabriel, taking one of Sam’s hands in his own and lacing their fingers together.

 

“It’s a little lonely back there, huh?” Gabe asked with a smile Sam could hear. “We’ll switch off next time. But for now I’d really like it if you started moving.”

 

Sam chuckled and started rocking his hips. Jess waited a moment to catch his rhythm then began as well. Gabe bit his lip, his eyes nearly rolling back in his head.

 

“Fuck – this feels incredible,” he sighed, sliding his free hand up Jess’ sides to cup her breast again. “You two are amazing.”

 

Once Gabe moved his hand, Sam rested his free hand on Jess’ hip. Jess purred and rocked her hips a little faster in Gabe’s lap. Sam squeezed Gabe’s hand and matched Jess’ speed. Gabe whimpered as they both moved, Sam inside him and Jess around him.

 

“Shit,” Gabe whined, sliding his hand down between Jess’ legs to rub her clit. “I’m so fucking close,” he panted, then chuckled breathlessly. “Usually I have more stamina than this.”

 

Jess giggled, leaning down to kiss him briefly.

 

“We believe you,” she said, breath hitching as Gabe rubbed her clit.

 

Sam kissed Jess’ shoulders, barely able to keep a rhythm; he came with a moan a few thrusts later, resting his forehead between Jess’ shoulder blades. Gabe gasped and came a moment later with Jess following close behind. They all went still, catching their breath and leaning against one another. Gabe panicked briefly when Sam pulled out, worried that they were just going to leave and not speak to him again, like every other fuck he’d had since getting to school. When Sam just settled next to him, Gabe let out a huff of laughter, mostly at himself.

 

“Something funny?” Sam asked, raising an eyebrow as Jess got off of Gabe.

 

“Hmm – no,” Gabe responded, watching Sam’s hands as he took off his own condom and knotted it before dropping it in to the trashcan next to Gabe’s bed.

 

Gabe waited until Jess was comfortably reclining next to him before doing the same to his condom.

 

“You laughed,” Jess accused playfully, running her fingers down his chest. “So something must have been funny.”

 

“I’m like a hyena, I laugh when I’m nervous. And gorgeous predators like you definitely make me nervous,” Gabe replied with a smirk, stretching between them. “Are you two staying the night? You’re welcome to – I’m sure it’ll be more comfortable than both of you crammed in a dorm bed. Hell, you’re both so tall I’m sure even a dorm bed on your own is cramped.”

 

“Sure, we could stay the night. Tomorrow is Sunday anyways,” Sam shrugged, looking to Jess.

 

Jess nodded, resting her head on Gabe’s chest with a yawn.

 

“Sounds good,” she murmured, reaching for Sam’s hand.

 

Sam rubbed his thumb across her knuckles as she dozed off, smiling.

 

“She looks sweet like that,” Sam said, sliding closer to Gabe.

 

“She does,” he replied, pulling Sam down to lay against the other side of his chest.

 

“I’m bigger than you,” Sam protested.

 

“And I’m older than you. Age and beauty before just beauty, kiddo – this is how we’re sleeping.”

 

Sam grumbled, but it was mostly for show. He curled closer to Gabe and closed his eyes, sighing happily. He fell asleep quickly, still holding Jess’ hand. Gabe held them both close and eventually drifted off to sleep. He felt like the luckiest guy on earth (or at least the luckiest in Palo Alto).

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

After breakfast in bed provided by Gabriel and a lazy day around the house, Sam and Jess headed back to campus to try to get some homework done before Monday rolled around.

 

“So,” Sam started, looking over at Jess. “Think that’s worth doing again?”

 

She nodded with a grin. Sam kissed her.

 

“I take it you liked it, then?”

 

“Yeah. I think this could be something really good, Sam.”

 

He nodded, giving her a kiss. “I think so too. I’ll talk to you later, I have another paper for Professor Summerhayes that’s due at midnight. I really have to get that done.”

 

Jess kissed him back. “I love you.”

 

“I love you too,” he said, smiling as he turned to go back to his dorm.

 

Jess whistled the whole walk back.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

Gabe felt like he was walking on air the rest of Sunday, even in to Monday. He hated Mondays, but not this one.

 

“What’s got you so chipper? Usually you hate Mondays more than Garfield,” Chuck commented as he nursed his third cup of coffee of the morning, still wearing the clothes he slept in.

 

“I resent that. I’m neither fat nor a cat,” Gabriel huffed, dumping three packets of sugar into his mug at the same time. “But if you must know, I had a nice weekend with Sam and Jess.”

 

“You had sex with them,” Chuck clarified.

 

“Well – yeah. But that wasn’t _all_ we did. I think I really like them. So get used to seeing them around here, Chucky boy,” he said with a wink, but it was clear to Chuck that the feeling was genuine.

 

“It’s nice to see you maintaining a relationship for more than one night,” Chuck said, smiling as he washed the morning dishes. “There’s nothing wrong with one night stands, but I know you were looking for something more. You’re not as subtle as you think.”

 

Gabe stuck his tongue out, looking for his playwriting textbook in the pile of miscellaneous items in their living room.

 

“Have you seen my playwriting book? I swear I left it here…” he trailed off, pushing the pile with his foot. “I think our house eats things.”

 

“Maybe one of your lovebirds took it by accident?”

 

“They didn’t have anything with them when they came or left, besides a bottle of wine.”

 

“It’d be a good excuse to text them though,” Chuck provided when Gabe didn’t seem to catch on. “C’mon, I thought you were smoother than this.”

 

“You of all people know I’m not a smooth guy – I just play one on TV.”

 

“Shut up and text them. Play the whole ‘oh no I think one of you has my textbook, can I come over and look for it?’ card. If you’re lucky, they’ll know they don’t actually have it, but think you’re cute anyways.”

 

“Fine,” Gabe grumbled, texting Sam and Jess and getting a response from Sam pretty quickly.

 

_i don’t think either of us have it. we’re studying in the library if you want to come join us. back corner of the reading room._

“They invited me to come study with them,” Gabe said, looking down at this phone.

 

“Then go, dipshit.”

 

Gabe didn’t need to be told twice.

~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

He practically ran into the library and only slowed down when one of the librarians at the circulation desk glared at him. He winked at her and went to find a map; he did most of his studying at his own house nowadays, he didn’t quite remember where the reading room was. A quick scan of the map and he was off again, sliding into the reading room and smiling when Jess waved at him from the table she and Sam were seated at.

 

“Hey,” he whispered, sitting with them.

 

Jess kissed his cheek, carefully moving some of the books she and Sam had spread out on the table to give Gabe some room to work.

 

“Sorry for the mess. Did you find your book?”

 

“Not yet, but I’m pretty sure it’s somewhere in my house.”

 

“Why’d you ask us if we had it?”

 

“An excuse to come see you.”

 

Sam snorted, looking up from his book.

 

“What? It worked, didn’t it,” Gabe said with a smirk.

 

Sam rolled his eyes, throwing his eraser at Gabriel playfully.

 

“You’re an ass.”

 

“Pulling out the pet names so soon, Sammy? I thought it would take longer with you.”

 

Sam grumbled and looked back at his book; Jess giggled, earning them a deliberate shush from the monitor on duty. Jess covered her mouth to muffle her giggles, eventually quieting down, but not quickly enough to avoid the scathing glare of a few of the other students around them.

 

“You are definitely my kind of girl, Jessica,” Gabe smiled, slinging an arm around her shoulders. “Don’t have a stick up your ass like Sam does.”

 

“You certainly didn’t mind having a stick up your ass Saturday night, Gabriel,” Sam countered with a smirk while taking notes on his reading.

 

“Touché, kiddo.”

 

Jess leaned against Gabe as she continued to read her textbook, sighing.

 

“I don’t know how much more of this I can take. It’s so _boring_ ,” she whined.

 

“I could make it more interesting,” Gabe whispered in her ear. “Give me the word and I’ll get under the table and eat you out.”

 

Jess turned pink. Sam noticed and kicked Gabe under the table.

 

“Fuck,” he shouted, reaching down to rub his shin. “What was that for?”

 

“We’re here to study, not to have sex. That can come later.”

 

After Gabe’s little outburst the monitor came over and asked them to leave. Sam grumbled as he packed his bag; Jess and Gabe couldn’t stop giggling as they all walked out.

 

“I hate you guys,” Sam said as soon as they were out of the building.

 

Jess leaned up to grab a kiss.

 

“No you don’t – you love us.”

 

He side-eyed Gabe then begrudgingly nodded.

 

“I’m just gonna go study in my room – see you guys around,” Sam said, heading back towards his dorm.

 

Gabe frowned a little and looked to Jess who gestured for him to go see Sam. Gabe rushed after him and practically jumped to kiss his cheek.

 

“Sorry,” he apologized, looking genuinely worried that Sam might be mad.

 

“It’s fine. It was kinda funny, if you’re into that sort of thing,” Sam shrugged. “Don’t worry.”

 

Gabe smiled and Sam leaned down to kiss him.

 

“I’ll talk to you later, Gabe,” Sam said as he continued on his way.

 

Gabe grinned and kissed Jess before heading to class.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

A month passed, full of simple dates and laughter. Gabe thought it might be the happiest he could remember being. Sam and Jess spent the night in his bed most weekends and despite some minor issues of jealousy that were quickly resolved with reassurances from the other two, everything was good.

 

“What exactly are you three?” Chuck asked Gabe one afternoon as they were watching the Food Network.

 

“What do you mean?” Gabe replied, petting Tiny absently.

 

His phone dinged and he checked it, smiling at a text from Jess, but not replying right away.

 

“Well – are they your boyfriend and girlfriend? Your lovers? Just friends you have sex with sometimes? Have you guys talked about this at all?”

 

“I…” Gabe frowned. “We haven’t talked about it. I don’t know what they consider us – I guess if I had to choose, I’d say we’re more than lovers. Maybe not boyfriends and girlfriends and all that, but more than just the occasional fuck.”

 

Chuck nodded, worrying his lip between his teeth.

 

“Sorry for bringing it up. Sounds like a touchy subject.”

 

“It’s fine. I just hadn’t thought about it,” Gabe murmured, lost in his own thoughts.

 

“Maybe you should ask them.”

 

“What if it scares them away?”

 

“I still think you should ask them. They’re probably wondering the same thing.”

 

“Maybe.”

 

Gabe didn’t respond to Jess’ text that night, too anxious about what their relationship should be labeled to deal with much of anything else.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

It was storming and Sam and Jess were at Gabe’s house. Classes were cancelled and the power was out all over town; it was more comfortable to wait it out with friends (or whatever their relationship had become, none of them were sure what to call it and no one wanted to be the first to offer up a label lest the other two not feel the same). Sam was stretched out on the couch, languid and reading comfortably with his head in Gabe’s lap. Jess was curled up in a pile of pillows on the ground nearby with Tiny sleeping next to her. Gabe ran his fingers through Sam’s hair, smiling at the contented noise the younger man made.

 

“You guys are adorable, y’know that?” he asked, brushing a thumb over Sam’s cheekbone affectionately.

 

Sam huffed something that sounded like “’m not cute” into the pages of his book, but it got lost in the ink and paper. Gabriel chuckled.

 

“Maybe we could do something besides just sit around? I know the rain is making you two into lazybones, but maybe we could do something simple like play a board game?” Gabriel suggested, looking over at the bookcase across the room. “I’m sure we could find something fun.”

 

Jess nodded, stretching and getting up to look at their choices.

 

“Well, it looks like you have half a chess set – the black half, monopoly with no money, some playing cards, and Scrabble,” she listed off, turning back to look at them.

 

“We played Go Fish last week – Scrabble it is!” Gabe grinned, nudging Sam.

 

Sam sat up and slid himself onto the ground, leaning back against the couch. “Scrabble I can do.”

 

“If we’re going to play a nerdy game then we at least need to make it _fun,”_ Gabriel said as Jess took out the board and dealt the tiles.

 

Sam groaned; he knew exactly what that meant.

 

“We’re not playing Strip Scrabble, Gabriel. I refuse.”

 

“Yes, we are.”

 

“C’mon, Sam, don’t be such a grouch. It won’t be so bad,” Jess said, leaning over to kiss the tip of his nose.

 

“Fine. How the hell would Strip Scrabble even work though?” he asked with a laugh, kissing Jess.

 

“Well – lowest score from the round loses a piece of clothing. If you spell a dirty word, you can make someone else take something off. Simple, right?”

 

“Why do we even bother with playing board games when we just end up naked? Why don’t we just start naked and save the fuss,” Sam grumbled, looking at the tiles he had been dealt.

 

Gabriel pouted. “You just don’t understand the intricacies of stripping games, Sammy.”

 

“Strip Go Fish was anything but intricate,” Sam replied, rolling his eyes.

 

Gabriel leaned over to whisper in his ear. “Yeah, but afterwards I rode your cock until you could hardly breathe. Don’t give me that bullshit, Sam Winchester, you love stripping games.”

 

Sam’s cheeks flushed and he worried his lips between his teeth. “Fine, we’ll play the fucking game.”

 

Gabriel grinned and kissed his cheek. “And maybe after the game we can do some fucking.”

 

Sam chuckled at that, watching as Gabe and Jess took their turns then placing his own tiles on the board. Sam ended up with the lowest score (“ _Dog? Really? You couldn’t have done better than that?”_ Gabe had mocked with a grin) and unbuttoned his shirt as Gabe took his second turn. Gabe ended up spelling _cock_ and grinned at Sam.

 

“Undershirt off too, Sammy.”

 

Sam rolled his eyes and pulled his undershirt off as well, leaving himself bare-chested. Gabe wolfwhistled and Jess kissed his cheek.

 

“I think I need a drink,” Sam muttered.

 

Gabe got up and grabbed some beers from the fridge, popping them open and handing one to each of them.

 

“Ready to play again, kiddo?”

 

“As ready as I’ll ever be.”

 

“That’s the spirit,” Gabe proclaimed, smacking Sam on the back in mock congratulation.

 

“You’re going to be the death of me.”

 

“Oh, but it’ll be a fun trip to the end.”

 

“Let’s just keep playing.”

 

In between drinking and spelling out the most complicated and dirtiest words they could manage, Sam lost both his socks and his pants, Jess lost her shirt and socks and Gabe was down to his undershirt and boxers.

 

“Do we really have to finish the game? We could stop now and have more time together in bed,” Sam suggested.

 

“Don’t whine because you’re losing. We’re finishing the game. It’s impolite to start something and not see it through ‘til the end.”

 

Sam snorted.

 

“ _You’re_ going to try to lecture me on being impolite Mr. So-Fucking-Annoying-We-Got-Kicked-Out-Of-The-Library?” Sam said incredulously.

 

“Hey – you said you thought it was funny.”

 

“That doesn’t make it polite.”

 

“Fine. I’m not polite. But we should finish the game anyways.”

 

Jess rolled her eyes, smiling at them.

 

“Honestly, I think if I wasn’t here you two would murder each other. Or just have angry sex all the time,” she said affectionately, leaning over the board to kiss them both on the cheek.

 

Gabe smiled, kissing her back.

 

“Wouldn’t be so bad. A little hatefuck never hurt anybody.”

 

Sam ignored him and played his tiles, gesturing for Gabe to take off his undershirt as he had the lowest score of the round. After a few more rounds, Sam was the first one completely naked thanks to Gabe getting a stroke of luck and playing the word _fuck_.

 

“I don’t even know if I can finish the game now – I’m awfully distracted by what I have to look at now,” Gabe said with a low whistle, looking Sam up and down.

 

Sam stood up and gathered the empty beer bottles to recycle, heading to the kitchen. Jess and Gabe watched him walk away.

 

“Hate to see you leave, but damn do I like watching you walk away,” Gabe commented, licking his lips.

 

Jess laughed and rolled her eyes, starting to put the game away.

 

“I think we’re done here – let’s go to the bedroom?”

 

Gabe nodded, standing up and helping Jess up. Offering Sam his free hand they headed back to the bedroom.

 

“What should we do today? I could fuck you while you eat Jess out,” Gabe suggested with a wink at Sam.

 

“I don’t know,” Sam responded, trying not to look as nervous as he actually was about the idea of being the one getting fucked rather than the one doing the fucking for the first time.

 

“If you’re not comfortable we don’t have to do it, Sam,” Gabe reassured, expression serious for a change. “I’m not gonna make you do something you don’t want to do and I’m sure Jess feels the same.”

 

“I wouldn’t mind trying it. But I can’t promise we’ll finish it. I don’t want to be impolite,” Sam said.

 

“No, we wouldn’t want that,” Gabe replied, kissing Sam’s cheek. “But if you want to try, I’ll go real slow and you’ll have Jess to distract you too. So what do you say, kiddo? Want me to fuck you?”

 

Sam nodded. Gabe smiled and helped Jess finish getting undressed first, letting her lay down on the bed before even beginning with Sam.

 

“All right. I’m gonna walk you through every step as we go, Sam. And if anything makes you uncomfortable you just tell me and we can pause or stop or whatever would make you feel best. Okay?”

 

Sam nodded again. For as much flack as he gave Gabriel, he had come to trust the other man over the course of their relationship so far. Jess certainly trusted Gabe and Sam trusted Jess, so Sam figured he could trust Gabe.

 

“Great!” Gabe smiled, nudging Sam towards the bed. “On your hands and knees so you’re in a good position to eat Jess out.”

 

Sam got on the bed, settling on his hands and knees and leaning down to nuzzles Jess’ folds. Jess purred; Gabe smirked.

 

“Not just yet, Sammy. I need your attention on me while we get started, then you can make Jess feel good.”

 

Sam pulled back, smiling sheepishly up at Jess. Jess pet his hair and caressed his cheek.

 

“I think – if you’ll let me – I’d like to rim you first. How’s that sound, Sam?”

 

Sam hesitated then nodded. Gabe kissed the small of his back and pushed his legs a little further apart.

 

“Might feel a little weird at first, but I promise it’ll be good,” Gabe murmured, spreading Sam’s cheeks. “You’re fucking gorgeous.”

 

He leaned in and pressed soft kisses to Sam’s hole. Sam let out a soft gasp; Gabe took that as an invitation to do a little more, licking a stripe over his hole before coming back and teasing him by circling the rim. Sam whimpered, pushing his hips back a little. Holding Sam’s hips still, Gabe pressed his tongue inside trying to get Sam to loosen up a little and relax. When Sam whined and clenched up a little, Gabe pulled back.

 

“Hey. Relax, kiddo. It’ll be so much easier if you relax,” he said soothingly, rubbing Sam’s hips.

 

Jess pulled Sam’s chin up a little to meet her eyes.

 

“Just look at me, Sam. Look at me,” Jess said, stroking his cheek.

 

He smiled at her gratefully.

 

“You can start again, Gabe. Sorry.”

 

“I’m gonna prep you with my fingers now. One to start and I’ll go as slow as you want me to,” Gabe said, leaning over to grab the lube out of the drawer. “You ready?”

 

Sam nodded with more confidence this time. Gabe started by rubbing Sam’s hole with just the tip of his finger before beginning to push it in. He stopped every half inch or so to give Sam a moment to breathe; he waited for a nod each time before continuing.

 

“Maybe you should start on Jess now,” Gabriel suggested, still working him open with one finger and a generous amount of lube.

 

Sam eagerly leaned down and started licking Jess, happy to have something to distract him. Jess smiled, running her fingers through Sam’s hair.

 

“You’ve always been so good at this,” she purred as Sam licked her clit.

 

Sam hummed against her as Gabe continued to stretch him open, adding a second finger only after he was sure Sam would be okay. He scissored his fingers inside Sam to stretch him even more, earning a whine against Jess’ pussy from the larger man. Gabe grinned, emboldened by Sam’s reaction, and crooked his fingers up to find Sam’s prostate. When Sam’s hips snapped forward and he moaned, Gabe knew he found the right spot. Sam pulled back from Jess a little, panting.

 

“That feels so good,” Sam said, pushing his hips back towards Gabe before leaning back in to pleasure Jess.

 

Gabe smiled and continued to stretch Sam open, adding a third finger just to be safe.

 

“Just tell me when you think you’re ready,” Gabe said, still working on Sam.

 

“Ready. Please,” Sam supplied quickly before licking Jess again.

 

“So polite,” Gabe replied with a grin, dragging his fingers out and wiping them on a tissue before pulling a condom out of the drawer and rolling it on. “If something feels bad just tell me to stop and I’ll stop.”

 

Sam nodded as best he could from his position between Jess’ legs. Jess whimpered, tugging his hair a little. Gabe slicked his cock with lube and lined up, pressing just the head against Sam’s hole so he could prepare before starting to push in. Sam whined against Jess, doing his best to stay relaxed.

 

“You’re doing so good, Sam,” Gabe murmured, rubbing his hips.

 

He pushed all the way in, taking his sweet time to make sure Sam felt as little discomfort as possible. Sam kept licking and sucking Jess; she came before Gabe was even done pushing in.

 

“Fuck, Sam,” Jess panted, tugging his hair.

 

Sam pulled back for a moment, looking up at her.

 

“I didn’t say stop,” she smirked, pushing his hair out of his face. “You know better than that, Sam.”

 

Sam smirked right back and got back to work again. Gabe started rocking his hips, keeping his thrusts shallow at first. Once Sam began pushing his hips back against Gabe with each thrust Gabe started to go harder and deeper. Sam moaned against Jess, shaking a little with each thrust. He came with a whine after a little longer, making a mess of the sheets. Jess clutched his hair and came right after him, followed by Gabe who gripped Sam’s hips so tightly there might be bruises in the morning.

 

Sam slumped down, resting his cheek against Jess’ stomach; Gabe carefully pulled out and let Sam’s hips follow the rest of his body down to the mattress. He took the condom off and knotted it before tossing it in the trash.

 

“How you doing, kiddo? Holding up okay?”

 

Sam mumbled against Jess’ skin, making her giggle at the sensation. He rolled over a little so he could be heard.

 

“’m fine. That felt really good,” he said with a lazy smile. “I think I’m gonna be sore in the morning though.”

 

“It’s a good sore,” Gabe countered, settling down with them.

 

Jess ran her fingers through Sam’s hair, humming contentedly.

 

“Y’know, Gabe – we don’t know a lot about you. Maybe you’d be willing to share some things with us? Doesn’t have to be anything big, but – something. Only if you want to,” Jess said, still petting Sam’s hair.

 

Gabe nodded a little, furrowing his brow as he tried to think of what to tell them.

 

“Well, for starters, I think I already mentioned it, but I had a complicated childhood. I never really knew my mom and my dad was a deadbeat alcoholic. I’ve got four siblings – two older brothers, Michael and Luke,” he paused to chuckle dryly. “Short for Lucifer, and two younger siblings, Castiel and Anna. We all took care of each other until Michael and Luke left for school. I only stuck around long enough to graduate and make sure Cas and Anna could handle themselves before I hightailed it here. Hell, I even hitchhiked most of the way. I wanted out. I’ve only heard from little Cas and Anna since I left – they’re both living with our uncle Balthazar and they’re both graduating this year – but I don’t even really talk to them much,” he sighed. “Closest thing I’ve got to family is Chuck and Kali. But Kali is thousands of miles away on the east coast and here I am on the west.”

 

Jess nodded, leaning over and kissing his cheek.

 

“How about yourselves?” Gabe asked with a small, sad smile after a moment. “As tragic as me?”

 

“I never knew my mom either,” Sam piped up. “She died when I was less than a year old. I think my dad and your dad could be friends – both being deadbeat alcoholics and all,” he sighed. “I’ve got one brother - Dean. Haven’t talked to him since I left. I know he’s mad at me for walking out, but I couldn’t take the pressure to take up the family business any longer. So here I am. I don’t know if I’ll ever see them or talk to them again. Only thing I’ve got left like a family is my not-really-my-uncle Bobby who keeps me updated on whether or not Dean’s alive. And you guys,” he finished, smiling a little.

 

“How about you, Jess?” Gabe asked her.

 

“Nothing to tell, really. My family is pretty normal. I still talk to my parents, though I don’t see them a lot because they’re back on the east coast. I don’t have any siblings,” she shrugged. “They wouldn’t be happy if they knew I wanted to study creative writing instead of something more practical, but they don’t have to know until I graduate if I switch majors,” she said. “Nothing tragic here, just good ol’ fashioned teenage rebellion while I can still get it in.”

 

Gabe kissed her; Sam slid up from where he was lying to get in a more comfortable position between Jess and Gabe. Gabe looked between them and smiled.

 

“I’m real glad we have this,” he said softly, resting his head on Sam’s chest. “You two have become real important to me real fast,” he continued, cheeks turning a little pink.

 

Sam wrapped an arm around him, then around Jess when she did the same on the other side of his chest.

 

“You’re important to us too,” Jess emphasized, leaning over to kiss his cheek.

 

He smiled and closed his eyes. They all drifted off quickly after the excitement and emotional payload of the night.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

Gabe was the first one up the next morning, stretching and easing his way out of Sam’s hold. He kissed them both on the forehead and went to clean up the house a little. Quietly making his way down the hall to avoid waking anyone, he picked up everyone’s discarded clothes and brought them back to the bedroom. He slid on a clean pair of boxers and went to grab a t-shirt before catching sight of Sam’s hoodie. He waffled for a second before grabbing it and putting it on. It was warm and soft and smelled like Sam (and a little like Jess too – she had probably done the same thing he was doing many times before); he never wanted to take it off. He smiled, keeping his hands inside the too-long sleeves and going to start breakfast.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

A big exam week came and they all barely saw each other for seven long days. Gabe’s king bed had never felt lonelier than it did that weekend, the first in months that it didn’t have two other warm bodies in it. He nearly didn’t have the energy to audition for the spring musical, but a text from Sam and Jess telling him to break a leg and that they were sure he’d do great got him going. He thought the audition went well enough, better than usual even, but he tried to push it to the back of his mind and finish his exams.

 

He called Kali after his last exam of the week, hoping she’d have something encouraging to say.

 

“What did I say about calling me more often, Gabriel?”

 

“Sorry, sorry. Things have been going really well with Jess and Sam. I didn’t think.”

 

“I guess I’ll take that excuse,” she said, but Gabe could hear the smile in her voice. “I’m glad things are working out for you, Gabriel. They sound like good people, from the little you’ve bothered to tell me.”

 

“They are!” he exclaimed, then checked himself. “Sorry. They are. They’re incredible, honestly. I can’t believe they’re still hanging out with me. Which brings me to why I called…”

 

“You only ever call when you need something,” Kali sighed, looking out at the autumn leaves swirling on the streets of Cambridge.

 

“I know. I know, I’ll be better about it. I just – need something amazing. We all just had a shitty week of exams and I want to be able to have something really nice with them. They’ve been eating my terrible homecooked meals a lot and I’m sure they appreciate it, but I think they deserve something better now.”

 

“Something romantic, then?”

 

“Yeah. Yeah, romantic sounds good,” he replied, nearly taking some paper out to take notes before thinking better of it.

 

“Take them in to the city. Palo Alto is nice and all, but San Francisco is a world apart. Buy them a nice dinner, get them a little drunk, dress up, relax.”

 

“I can’t get them drunk in public, they’re underage. And I’m not exactly on a shoestring budget, but I’m not loaded either, Kali…”

 

“I’m sure you can figure something out, Gabriel. You weren’t rich in high school, but you still made some fairly large romantic gestures. You’re nothing if not innovative.”

 

He grinned, thinking back to what he had done back then.

 

“Okay. Yeah, I can do this. Thanks, Kali.”

 

“It’s really no trouble. Just call more often, Gabriel. People here are rather boring – I miss your stories.”

 

“I’ll call more, I promise. I love you.”

 

“I love you too. Now go woo your lovers or whatever they are.”

 

“I’ll do my best,” he said with a grin, hanging up.

 

He had three days to plan before the weekend. He texted Sam and Jess.

 

_saturday night, wear the nicest clothes youve got. its date night._

_~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~_  

He panicked the whole three days, researching restaurants in the city that they could go to. He settled on a place called AQ – they changed their décor and menu to match the seasons. It sounded interesting and he remembered Jess and Sam both mentioning that their favorite season was fall; he hoped he was making a good choice.

 

Gabe picked Sam and Jess up on campus in his old and beat-up Volkswagen Beetle. It was a disgustingly bright yellow, but somehow it was appropriate for Gabriel. He whistled at them, trying to mask his own nerves with flirting.

 

“You two clean up nice,” he said as they got in the car.

 

“Where are we going?” Jess asked as she settled into the back seat, Sam taking the front for the extra leg room.

 

“It’s a surprise.”

 

“Are you kidnapping us?” Sam asked, raising an eyebrow.

 

Gabe laughed.

 

“I could, if you’re into that,” he said, then winked at Sam. “It’s just a date – relax.”

 

They started on their way towards the city, mostly quiet for the first portion of the drive, Gabe concentrating on not freaking out and Sam and Jess wondering where Gabe was going to take them. Jess broke the silence.

 

“How was your audition, Gabe?”

 

“Huh? Oh. It was good. I – uh – I got a part, actually. Nothing major, of course, but a part.”

 

“That’s fantastic! When’s the play? We’ll come cheer you on or bring you flowers or whatever is appropriate for theater,” she said with a grin.

 

“It’s next semester, right before spring break. Hopefully people will be bored enough with classes by then to come see it.”

 

“We’ll be there for every performance.”

 

“Thanks. How did exams treat you guys?” Gabe smiled.

 

“I think I did okay. I _hope_ I did okay,” Jess shrugged. “I’m trying not to think about it right now.”

 

“Administrative Law kicked my ass,” Sam sighed.

 

“Isn’t that a class for actual law students to take, not pre-law?” Gabe asked, peeking over at him for a second before looking back at the road.

 

“Special permission from the dean,” Sam said with a smirk. “I’m regretting it now.”

 

“I’m sure you did fine, Sam,” Jess said, leaning forward from the back seat and kissing his cheek. “Don’t worry so much.”

 

They spent the rest of the drive making small talk about exams and life in general from the past week; Gabe cursed as they looked for a parking spot.

 

“I should have known better than to try to park in the city,” he grumbled, finally finding a spot and pulling in.

 

They headed down the street towards the restaurant with Gabriel leading the way. Jess took Gabe’s hand with a smile and offered Sam her other hand. Sam raised an eyebrow, looking around.

 

“Nervous someone will hate crime us, kiddo?” Gabe asked with a grin to cover up his own nervousness.

 

“A little.”

 

“I doubt anyone will even notice us,” Jess said, lacing her fingers together with Sam’s. “Relax.”

 

He smiled a little and kissed Jess’ cheek; they found the restaurant and Gabe led them in, checking their reservation at the hostess station. They were seated quickly. Jess looked around, smiling.

 

“It’s beautiful in here – looks like fall back home. The leaves don’t really change as much here,” she said softly, still looking at the décor.

 

“Yeah, they change the décor and menu based on the seasons in New England where the owner is from. I thought it’d be interesting,” Gabe said with a shrug.

 

Jess smiled, kissing his cheek. They all looked over their menus

 

“Get anything you want – I’m buying,” Gabe said before the waiter came back to take their orders.

 

Gabe ordered petrale sole (and an applejack cocktail with a shrug like he would try anything once), Sam got veal with charcoal and Jess decided on duck confit. Sam smiled a little.

 

“This is – fancier than I’m used to,” he said quietly, looking from the fake trees with autumn leaves to the decorative copper on the walls.

 

“I thought it’d be a nice change of pace from whatever they serve in the campus cafeteria,” Gabe replied with another shrug.

 

When their food came they didn’t talk much, all enjoying what they had ordered.

 

“You want to try some?” Sam asked Jess, offering her some of his meal.

 

She smiled and tried a bite, giving Sam a taste of hers too. Gabe pouted and Jess smirked, offering him some as well. By the end of the meal they had all had nearly equal amounts of their own and the other two meals. Sam and Jess each had a taste of Gabe’s drink as well.

 

“It’s too sweet,” Sam said with a little grimace. “And I feel like a kid, sneaking a sip of your alcohol so we don’t get thrown out.”

 

Jess rolled her eyes and bumped her knee against Sam’s under the table.

 

“Don’t be so whiney,” she chuckled, trying some of Gabe’s drink. “And it’s not too sweet – it tastes just like the cereal.”

 

They finished their meals and ordered a sweet potato pie for dessert. Gabe smiled while they ate dessert, playing footsie with both of them under the table. Jess giggled; Sam rolled his eyes, but he couldn’t help his smile. They finished their meal and Gabe paid and tried not to think too much about how much he just spent on a meal for three (he reminded himself that it really was incredible and that Jess and Sam looked really happy).

 

They spent some time walking around downtown San Francisco. Jess tried on and bought a new purple dress that made her look stunning. Gabe insisted on buying them both flowers from a street vendor. Sam turned as red as the rose Gabe gave him; they both kissed Gabe. After a bit more walking and a yawn from Jess, they found Gabe’s yellow Beetle and made their way back to Palo Alto.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

Sam and Jess stayed the night and through the next day, just spending lazy time together relaxing the unusually warm autumn sun. Sam took a nap with a book on his chest in the backyard. Jess and Gabe played fetch with Tiny. Gabe “tripped” and fell on top of Sam, grinning when Sam flinched and opened his eyes to glare at him.

 

“You’re an ass.”

 

“Hey, it was an accident,” Gabe replied indignantly, kissing Sam.

 

“I don’t believe you,” Sam replied, kissing Gabe back.

 

“I swear to whoever is up there that it was an accident.”

 

“You don’t believe in that,” Sam smirked.

 

“No, I don’t,” he replied with a shrug, sitting up a little and wiggling his hips in Sam’s lap before jumping off of him and running to Jess. “And it wasn’t really an accident either.”

 

Sam rolled his eyes, getting up to put the book away.

 

“You’re going to pay for that someday, y’know,” Jess said, leaning against Gabe. “He’s like an elephant or something, he never forgets.”

 

“He’s like an elephant in a lot of ways – he’s huge and clumsy too.”

 

Jess laughed, pushing Gabe playfully.

 

“Rude!”

“No one ever said I was polite,” he responded, kissing her.

 

“No. Polite can be boring though,” she said with a smile, kissing him back.

 

Gabe smiled, holding her close and waving to Sam to come over when he came back outside.

 

They made love in Gabe’s backyard, giggling the whole time, neighbors be damned. They showered together afterwards – it was crowded, but they made it work. Gabe even discovered that Sam and Jess both liked getting their hair washed. He filed that knowledge away for later, in case he ever needed to do something to make up for something he fucked up.

 

None of the three could stop smiling.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ 

They cooked dinner together that night, Jess in charge because she had the most experience in the kitchen. By the time they were ready to eat they and the kitchen were a mess, but they were all laughing and kissing enough that they didn’t care so much about the mess. They ate in the backyard, watching the sun set behind the trees.

 

After eating they had some wine and just relaxed together. Gabe reclined in the grass, putting his arms behind his head and looking up at the stars. Sam shrugged at Jess and they both joined him on the ground.

 

“It’s so clear out tonight. It’s really beautiful,” Jess murmured, looking at the full moon and the stars above them.

 

Gabe unfolded his arms from under his head and pulled them both closer.

 

“Almost as beautiful as you two,” Gabe said with a smile, kissing them both on the cheek.

 

They smiled; Sam pointed out a few constellations he remembered from his times laying on the hood of the Impala with Dean, watching the night sky. They were silent for a while after that, just enjoying the view and each other’s company.

 

“Angelo,” Gabe said softly, out of the blue.

 

“What?” Sam asked, turning a little to look at him.

 

“It’s my last name. Hardly anyone here knows, I sorta made a point of it. I don’t know why – I guess I just thought I could start anew if no one knew my name. Kinda stupid,” he shrugged, sighing. “I just thought you guys should know.”

 

Sam and Jess smiled, kissing his cheeks simultaneously.

 

“We love you too,” Jess said, replying to what Gabe left unsaid.

 

Gabe turned a little pink and kissed them both, murmuring “I love you” quietly against their lips.

 

They might not know where they’re going or what they’re going to do with the rest of their lives, but they knew they wanted to do it together.

 

 

**Author's Note:**

> Written for the Gabriel Big Bang challenge! My first big bang and my first polyamory fic (though I've been wanting to write them for a while)! Thanks to all my betas, my roommate who dealt with me freaking out the whole time I wrote this and to my artist~
> 
> Title taken from The Great Gatsby.
> 
> Come talk to me on Tumblr about Sam/Gabe/Jess - I'm queerbriel over there!
> 
> Amazing art over here: http://queerpanic.tumblr.com/post/83611558165


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